(2-aminophenyl)(3,4,5-trimethoxyphenyl)methanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-aminophenyl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: (2-Aminophenyl)-(3,4,5-trimethoxyphenyl)methanone
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: UUWNPIZRFIINAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-3,4,5-三甲氧基苯 在 盐酸 、 重铬酸吡啶 、 铁粉 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2-aminophenyl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of 2-Aminobenzophenone Derivatives as Antimitotic Agents

  摘要：

  A new type of inhibitor of tubulin polymerization was discovered on the basis of the combretastatin molecular skeleton. The lead compounds in this series, compounds 6 and 7, strongly inhibited tubulin polymerization in vitro and significantly arrested cells at the G(2)/M phase. Compounds 6 and 7 yielded 50- to 100-fold lower IC50 values than did combretastatin A-4 against Colo 205, NUGC3, and HA22T human cancer cell lines as well as similar or greater growth inhibitory activities than did combretastain A-4 against DLD-1, HR, MCF-7, DU145, HONE-1, and MES-SA/DX5 human cancer cell lines. Structure-activity relationship information revealed that introduction of an amino group at the ortho position of the benzophenone ring plays an integral role for increased growth inhibition.

  DOI：

  10.1021/jm010365+

文献信息

• Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles
  作者：Jiuxi Chen、Leping Ye、Weike Su

  DOI：10.1039/c4ob00978a

  日期：——

  A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L−1 and 0.09 μmol L−1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L−1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target.

  开发了一种钯催化的芳基硼酸与未保护的2-氨基苯腈直接加成反应，得到了一系列中等至优异收率的2-氨基二苯甲酮。该反应具有广阔的应用范围和高度的官能团耐受性。此外，2-氧代吲哚啉-7-腈和吲哚-7-腈也适用于该过程，分别用于构建7-苯甲酰基-2-氧代吲哚啉和7-苯甲酰基吲哚。在检测的化合物中，化合物4e对H446和HGC-27细胞具有最强的体外抗癌活性，IC50值分别为0.02 μmol L−1和0.09 μmol L−1，而化合物4a对SGC-7901细胞显示出最佳的抗癌活性，IC50值为0.01 μmol L−1。此外，我们还进行了计算机分子对接计算，以研究检测化合物与其微管蛋白靶点之间的相互作用模式和结合亲和力。
• Phenyl substituted pyrido(1,4)benzodiazepines and intermediates therefor
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0076017A2

  公开（公告）日：1983-04-06

  [2-[(Aminopyridinyl)amino]Phenyl]aryl-methanones which also have antidepressant activity are used to prepare pyrido[1,4]benzodiazepines having antidepressant activity of the formula wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, loweralkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts thereof.

  具有抗抑郁活性的[2-[(氨基吡啶基)氨基]苯基]芳基甲酮可用于制备具有抗抑郁活性的吡啶并[1,4]苯并二氮杂卓，其式为 其中 Ar 是 2、3 和 4-吡啶基、2 或 3-噻吩基、苯基或取代苯基；R 是氢、低级烷基或烃链末端的胺；Z 是氢、卤素、三氟甲基、低级烷基、低级烷氧基、羟基或硝基；Y 是氢、低级烷基、低级烷氧基或羟基；以及它们的药用盐。
• Antiinflammatory derivatives of 3-aryl-2,1-benzisoxazole
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0260924A1

  公开（公告）日：1988-03-23

  Novel 3-Aryl-2,1-benzisoxazole compounds having the formula: wherein each R1 and R2 represents a hydrogen atom or methyl group; R3 and R4 represent a hydroxyl, loweralkoxy, amino or -OM group wherein M is a pharmaceutically acceptable cation; X represents a hydrogen or halogen atom, a loweralkyl or nitro group; Y represents a hydrogen or halogen atom, a loweralkyl, loweralkoxy, nitro or trifluoromethyl group; n and p are independently zero or one with the proviso that either n or p must be one are disclosed. which have anti-inflammatory activity. Novel intermediates in the preparation of such compounds are also disclosed.

  本发明公开了具有以下式子的新型 3-芳基-2,1-苯并异噁唑化合物： 其中每个 R1 和 R2 代表氢原子或甲基；R3 和 R4 代表羟基、低级烷氧基、氨基或 -OM 基团，其中 M 是药学上可接受的阳离子；X 代表氢原子或卤素原子、低级烷基或硝基；Y 代表氢原子或卤素原子、低级烷基、低级烷氧基、硝基或三氟甲基；n 和 p 独立地为 0 或 1，但 n 或 p 必须为 1。 本发明还公开了制备此类化合物的新型中间体。
• US4447361A
  申请人：——

  公开号：US4447361A

  公开（公告）日：1984-05-08
• US4495183A
  申请人：——

  公开号：US4495183A

  公开（公告）日：1985-01-22